1. Field of the Invention
This invention relates to bis-naphthalimides, processes for their preparation, pharmaceutical compositions containing them, and methods of using them to treat cancer in mammals.
2. Prior Art
Harnisch, et al. in U.S. Pat. No. 4,841,052 issued Jun. 20, 1989 describe naphthalic acid imides of the formula ##STR1## wherein: A.sup.1 represents C.sub.2 -C.sub.5 -alkylene,
K.sup.1+ represents ##STR2## R.sup.6 represents C.sub.1 -C.sub.16 -alkyl, carbamoylmethyl or benzyl; R.sup.7 represents methyl or ethyl or a single bond linked to D; PA1 R.sup.8 represents methyl or ethyl; PA1 W.sup.1 represents ##STR3## Z.sup.1 represents --CH.sub.2 --, or ##STR4## --O-- or --SO.sub.2 --; and X represents an unsubstituted benzosulphonate or a benzenesulphonate substituted by chlorine or C.sub.1 -C.sub.12 alkyl, a C.sub.5 -C.sub.18 alkylsulphonate or a salt of a C.sub.5 -C.sub.18 alkylcarboxylic acid or a salt of a condensation product of formaldehyde and arylsulphonic acids and/or optionally sulphonated 4,4'-dihydroxy-diphenylsulphone, wherein D represents --CH.sub.2 --, --CH.sub.2 --CO--, --CH.sub.2 --CO-- PA1 HN--or --CH.sub.2 --CO--NH--CH.sub.2 -- and m represents 0 or 1. PA1 R.sup.2 and R.sup.3 independently are H, C.sub.1 -C.sub.6 alkyl; each A independently is O or S; PA1 X.sup.2 and X.sup.3 independently are H, CH.sub.3, phenyl, OR.sup.5, SR.sup.6, PA1 N(R.sup.7).sub.2, 4-hydroxyphenyl, imidazoyl or indolyl; PA1 X and Y independently are H, NO.sub.2, halogen, NHCOCF.sub.3, NHSO.sub.2 CF.sub.3, SO.sub.2 R.sup.8 or N(R.sup.9).sub.2 ; PA1 R.sup.5, R.sup.6, R.sup.8 and R.sup.9 independently are H, C.sub.1 -C.sub.6 alkyl; each p independently is 0-4; PA1 m is 0-4; PA1 n is 0, 2-12; and PA1 R.sup.7 is H or C.sub.1 -C.sub.6 alkyl, provided that each R.sup.7 in N(R.sup.7).sub.2 cannot both be H. PA1 X is H or NO.sub.2 ; and/or PA1 Y is H or NO.sub.2, provided that one of X or Y is NO.sub.2 ; and/or PA1 n is 2-4; and/or PA1 p is 0; and/or PA1 A is O; and/or PA1 R.sup.1 and R.sup.4 are CH.sub.3 ; and/or PA1 R.sup.2 and R.sup.3 are H. PA1 a) The compound of claim 1 which is (S,S)-N,N'-1,2-ethanediylbis[.alpha.-methyl-5-nitro-1,3-dioxo-1H-benz[de]i soquinoline-2(3H)-acetamide]. PA1 b) The compound of claim 1 which is (R,R)-N,N'-1,2ethanediylbis[.alpha.-methyl-5-nitro-1,3-dioxo-1H-benz[de]is oquinoline-2(3H)-acetamide]. PA1 c) The compound of claim 1 which is (S,S)-N,N'-1,2ethanediylbis[.alpha.-methylthioethyl-5-nitro-1,3 dioxo-1H-benz[de]isoquinoline-2(3H)-acetamide. PA1 d) The compound of claim 1 which is (S,S)-N,N'-1,4-butanediylbis[.alpha.-methyl-5-nitro-1,3-dioxo-1H-benz[de]i soquinoline-2(3H)-acetamide. PA1 e) The compound of claim 1 which is (S,S)-N,N'-1,3propanediylbis[.alpha.-methyl-5-nitro-1,3-dioxo-1H-benz[de]i soquinoline-2(3H)-acetamide. PA1 f) The compound of claim 1 which is (S,S)-N,N'-1,2ethanediylbis[.alpha.-methyl-5-nitro-1,3-dioxo-1H-benz[de] isoquinoline-2(3H)-ethanethioamide].
These compounds are highly suitable as chargeregulating substances in electrophotographic toners.
U.S. Pat. No. 4,874,863 issued Oct. 17, 1989 discloses anticancer compounds of the formula ##STR5## wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are identical or different and are each H, NO.sub.2, NH.sub.2, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, OH, C.sub.1 -C.sub.6 -alkoxy, halogen, trihalomethyl, C.sub.1 -C.sub.6 alkyl, formyl, C.sub.1 -C.sub.6 -alkylcarbonyl, ureyl, C.sub.1 -C.sub.6 -alkylureyl and R is a straight chain or branched C.sub.4 -C.sub.10 -alkylene which is interrupted at one or two points in the chain by a secondary or tertiary amino group, where 2 nitrogen atoms may additionally be bonded to one another by an alkylene group, or a salt with a physiologically tolerated acid.